


Wingmen

by imagining_supernatural



Category: Supernatural
Genre: Alternate Universe - High School, Deadpool - Freeform, F/M, Geez, High School, I wrote this when deadpool 1 came out, Implied Sexual Content, Implied Smut, fluff!, that was forever ago!!!
Language: English
Status: Completed
Published: 2020-03-31
Updated: 2020-03-31
Packaged: 2021-02-26 16:25:33
Rating: Teen And Up Audiences
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,839
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/23405263
Author URL: https://archiveofourown.org/users/imagining_supernatural/pseuds/imagining_supernatural
Summary: You're a tomboy and best friends with Dean Winchester. When you start going out on dates with your other friends, Dean gets a little jealous. High School AU
Relationships: Dean Winchester/You, dean wincheser/reader
Kudos: 22





	Wingmen

“You have _another_ date?” Dean asked, launching the basketball at you. You caught it easily and went for a lay-up.

“Yup.”

“Zach again?” He asked, a strange, detached tone in his voice.

“Nope. Remember, he got back together with that Sarah chick, or whatever. James asked me out this time, for some reason.” For as long as you could remember, you’d been _one of the boys_. They never tried to stop you from playing video games with them and you were the first to volunteer to do anything if it meant your mom would yell at you for getting mud on your clothes. But lately it was like everyone realized that puberty had been really good to you. They still knew that you could kick their ass in basketball and you could build a robot that would literally kick their asses, but they kept asking you out anyway. It was weird. “We’re going to see Deadpool on Friday.”

“Deadpool? How romantic,” Dean sneered, lining up a three-point shot. The ball circled the rim and almost went in, but momentum popped it back out. “When are we gonna work on our car?”

“Uh, Saturday? Dates typically don’t last all weekend, Dean.”

Dean chased after the ball and tried the shot again. When this one went in, he turned to you. “See you Saturday morning, then?”

You picked up the ball from where it had rolled to your feet and dribbled over to the free-throw line. As soon as the ball left your fingers, you knew it was a good shot. A second later, the chain net jangled. “Bright and early.”

* * *

“Two for Deadpool,” James tried to sound old enough to get in.

The man behind the glass just rolled his eyes. “Beat it, kid.”

“I’ll handle this,” you assured James. Turning all of your attention on the man, you glanced at his nametag and recognized him. “Phil, right? You worked with my mom a few years back on that town carnival committee thing?”

“Right! Y/N, it’s good to see you again!”

“Listen, this is our first date, and it’s either Deadpool or that one Nicholas Sparks movie. If we get into Deadpool, we’ll actually watch it. The other one and we’ll be so bored that we won’t have much good to do and we’ll end up distracting the other people in the theatre, which wouldn’t be good for your business.”

“Well, I don’t know,” Phil hedged, scratching his head.

“My mom already took me to see this movie last week. I promise we’ll act a few months older than we are and no one will know that you let in some sixteen year olds, okay?” Not that you were too far from seventeen, but rules were rules.

“I… I guess. That’ll be sixteen dollars.”

You turned to James victoriously and motioned for him to pay. You would have bought your own ticket, but his mother had insisted that you let him pay for everything. Once the two of you were alone, you told him you’d buy him lunch some other time, or something.

As James paid, you glanced around at everyone else and thought you saw some familiar green eyes, but the crowd shifted and you lost him. You shook your head. Why the hell would Dean be here? He already saw this movie with you.

James drew your attention back to him. “So it’s not just us that you confuse until we agree to something, huh?”

“It’s a skill I learned from my older sisters.”

“I remember them,” James mused as he led you into the theatre. “They ran the school when they still were here.”

“Yep.” Your sisters had been prom queens, student body presidents, and volunteered at any charity they could. And it wasn’t like they were just doing it to look good: they really were that amazing. “I toned down the flirting a bit, but I got the chatty Cathy part down.”

“So, did your mom really take you to this movie already?”

“Yeah. My parents invited the Winchesters and we made it a big family date thing.”

“And how was it watching the sex scenes while sitting next to your mom?”

You laughed. “You think Sam and Dean would let their parents sit by them in public? No, we made the adults sit at least seven rows away from us.”

The night felt more like you were hanging out with one of your friends, rather than on a date with him. The night ended with a hug and kiss on the cheek and an agreement that you were better off as just friends.

As you were heading into your house, you could have sworn you saw Dean’s car turning the corner.

* * *

“Did you like Deadpool just as much the second time?” You casually asked Dean as you bent over the engine to reach the transmission.

“What? I didn’t see it again,” Dean uncomfortably shifted. You just fixed him with a look that told him you didn’t believe him and held your hand out. He handed you a wrench and you set to work.

“Oh. I guess I just saw someone who looked like you, then.” Dean’s discomfort made you smile. All of the other guys seemed to notice you weren’t _just one of the guys_ anymore, except for Dean. And, for some reason, he was the one that you wanted to notice.

“What about you? How did the _date_ go last night?”

“Great,” you said with enthusiasm. If Dean was finally starting to get interested, you had to monopolize this time. “We had a blast, had some laughs, and Deadpool still ended up getting the girl.”

“And James?” Dean asked, looking away nonchalantly. “Did he end up getting the girl?”

_ Smooth, Dean_. You propped your arms on the edge of the frame and looked across the engine at Dean. “Since when are you into my personal life? Is it just ‘cause your family is gone and you’re bored?”

“I’m your friend. That’s what friends do, right?”

“Right,” you said slowly before returning to your work on the transmission. You added an open-ended statement offhandedly, “If friends is all you wanna be.”

“What was that?”

You looked up as innocently as you could. “Nothing. Hand me a Phillips.”

Dean did as you asked, but you could still feel your skin tingling where his eyes were watching as he puzzle out your last statement. The two of you worked quietly on the classic Firebird that Dean’s dad bought him for his sixteenth birthday just over a year ago. Ever since the grand unveiling, you and Dean had been working to fix it up.

An hour later, Dean came over and leaned against the frame. “You never answered my question.”

“What question was that?” You put the tools down and mimicked his pose.

“Are you and James a thing now or…?”

“No,” you shook your head slightly.

“Oh, okay,” Dean nodded and took a swig of the beer he’d stolen from his dad’s garage fridge.

You watched him for a second longer, trying to figure out what he was thinking. “You satisfied now?”

“What? Oh, yeah. His loss.” Dean shrugged off the car and stiffly walked to the front of the car. You returned to what you’d been doing, but kept him in the side of your vision.

“Dean?” You asked a few minutes later. “What did you mean when you said _his loss_?”

“I just…” His eyes widened in panic as he tried to think of a way around whatever he had been thinking. Then his shoulders relaxed and he strolled around the car to bend over the engine next to you. “Alex, Zach, James… all those guys who didn’t go for a second date with you were idiots. Anyone can see you’re one of a kind and…”

He trailed off and you waited for him to resume, but he didn’t. “And what? Don’t hold back now, Dean. You’ve never held back with me before. Don’t start now, especially when you’re complimenting me.”

An adorably shy grin came over his face as he looked down at the engine. Then he turned his head to face you. “You’re the full package, Y/N. You’re not scared of anything, you don’t care about your nails or clothes or whatever, but you’re still hot as fuck and you can make anyone laugh. Do you have any clue how much I hated watching you go out with our friends the last few weeks? It’s been hell.”

Silence fell as he ended his little speech. It took you a moment to fully register his words, and even when you did, you didn’t know how to respond. Your sisters would know what to do in this situation, but you had no clue. So you fell back on habit and picked something you could make a joke about.

“Exactly how hot is fuck? I don’t remember learning about that unit of measurement in school and this sounds like something I could put on my résumé or at least use when I forge letters of recommendation, but I think I should—“

Dean leaned forward and kissed you, effectively ending your rambling. He brought his hand up to your cheek, rubbing his thumb over your cheekbone. You sighed into his mouth and dropped the tools in your hand onto a tray so you could shift closer. You stood up, but a sharp pain surrounded the top of your head where it hit the hood and you pulled away from Dean, laughing.

“You okay?” He asked, his hands skipping over your head, trying to find where you’d hit it.

You just nodded and pulled him into you by his oil stained shirt. He quickly forgot about your head’s meeting with the hood and wrapped his arms around your back, pulling you tight against him. You could feel every inch of him, but not enough. You reached up until your fingers were linked behind his neck and you took the kiss deeper. He groaned, fingers digging into your hips.

“Just tell me when to stop,” he rasped against your lips just before kissing across your cheek and biting gently on your earlobe.

“Don’t count on it,” you moaned, pressing your hips into his, plans on working on the car completely forgotten.

Dean pulled back, his dark green eyes piercing yours. “Really?”

“Really,” you nodded, promising with your eyes.

He kissed you again and again, backing you up until your back hit the cool metal of his car. Heart racing, you slipped your hands under his shirt and flattened your palms against the warmth of his skin. Dean dropped kisses down your neck as he tugged at your ponytail until your hair came free. Panting, he looked at you. “Is this your…?”

“First time? No.” Knowing he would wanna know at least when, you explained, but didn’t reign in your hands as they explored his body. His own hands gripped your waist and his hips pressed yours back into the car. “Remember that reform church camp my parents sent me to for a month last summer because we almost got arrested for vandalism?”

Dean grinned. “You lost your v-card at a reform church camp? That’s my girl.”

_ My girl_. You tugged on the hem of his shirt until he got the hint and pulled it over his head. It wasn’t the first time you’d seen him shirtless, but it was definitely the first time you’d seen him shirtless like _that_. He watched you check him out with hooded eyes. “Like what you see?”

You bit your lip and laid a hand on his chest, trailing it down until it rested just above his jeans. “I think we should go to your room.”

Dean’s chest heaved and he caged you against the car’s frame again. “Why do that when we have a perfectly good backseat right here?”

“You wanna do it in your car?” You asked, though his suggestion had your mind playing out some very dirty fantasies about this car now.

“Hell yeah. We’ve worked on this car together. I think it’s only fair we christen it together, too.”

“Okay,” you grinned, framing his face with your hands and going up on your toes to kiss him. “Lead on.”

“First thing’s first,” Dean muttered, sliding his hands from the car to your shoulders, down your arms and sides, until they rested on the hem of your shirt. “I think there’s a no shirt rule in the car today.”

“Well, we can’t go breaking the rules, now can we? That’s just not who we are.” You pulled your shirt off with practiced ease and tossed it in the general direction Dean threw his. When you looked back at him, his eyes were completely overtaken with lust. He curved a hand around your waist and your skin burned where he touched you.

“You’re beautiful,” he whispered in your ear, just before sucking on the sensitive skin behind your ear. His lips met yours again and the two of you stumbled toward the back door. It creaked as Dean wrenched it open.

“We need to fix that,” he murmured distractedly as you climbed into his car.

“The car can wait.” Curling your finger, you motioned for him to join you. “I have some needs you need to help with first.”

With a dark grin, he climbed over you. “I’m always happy to help.”

Your lips met again and it wasn’t long before the two of you were lost in hot breaths, heavy panting, and hands slipping over sweaty skin.

* * *

“Y/N!” Tom called, jogging to catch up to you before school on Monday. “Hey, I was wondering what you were doing this weekend.”

“I—“ You glanced around and saw the rest of your friends watching the exchange with unveiled curiosity. Their eyes shifted to something behind you and you turned just in time to see Dean walk in the front doors. “Why?”

“I was thinking we could go out. That new ice rink is opening and…” he shrugged.

“Oh, well,” you looked over and saw that Dean had slowed his steps and was watching you with raised eyebrows. His family had been gone all weekend which gave the two of you plenty of time to talk and… explore your new relationship more. But one thing you hadn’t figured out was how to handle the new situation with your friends. After all, you had gone out with over half of them in the last month. “I think I have plans already, but thanks Tom.”

“Plans?” You missed the way his eyes gleamed and shifted to Dean for a split second. “With who?”

“Uh, Dean, actually.” You cheeks warmed and you rushed on, trying to give an explanation that wouldn’t give anything away. “We didn’t get much done on the car this weekend and—“

“Uh-huh. I bet,” Tom insinuated, wiggling his eyebrows.

You tilted your head, analyzing him for a moment. “You look incredibly smug for someone who just got turned down.”

Dean walked up, but was careful to keep his distance from you. “What’s up?”

“Tom asked me out, I turned him down, and now he’s… gloating?”

“Well,” Tom smirked, crossing his arms victoriously. “Why do you think we all waited so long before making a move on you, Y/N?”

“Puberty hit late then you were all chickens? I don’t know.”

The rest of your group of friends came over, identical grins on their faces. “We were giving that big chicken over there,” Alex nodded toward Dean, “A chance to man up and make his move. But he didn’t. So I did.”

“And you didn’t go for Alex,” Zach butted in, “So I thought I’d give it a try.”

“So what? I’m a piece of meat now?”

James shook his head emphatically. “You’re one of the coolest chicks we know and if nothing was gonna happen between you and Dean, we wanted to see if we could have a chance.”

“You guys are dicks,” Dean growled, taking a step closer to you.

“I don’t think my sisters’ girlfriends were ever this interested in their love lives,” you mused.

“Well, we _are_ called wingmen for a reason,” James grinned. “Just promise us you two won’t be that lovey-dovey gross couple.”

Your friends’ actions really sunk in and you just shook your head and sidled up to Dean’s side. You slid your arm around his back. “After what you guys just told me, I think you all deserve to be put through that for a few days, at least.”

Dean rested a finger under your chin, turning your face up to his. He fixed a _lovey-dovey gross _smile on his face and leaned down to kiss you. “I agree, _pumpkin_.”

“Ugh, no to the pumpkin,” you grimaced. “It’s supposed to be torture for them, not us.”

Dean laughed like normal. “Fine, sweetheart. But I’m all for making out.”

The boys all made various disgusted noises and excuses to leave, but you and Dean didn’t care. Nope, you and Dean didn’t care one bit.


End file.
